5-Acetylamino-4-hydroxy-2-methoxy-6-(1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid

ID: ALA1206203

PubChem CID: 15108907

Max Phase: Preclinical

Molecular Formula: C12H21NO9

Molecular Weight: 323.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@]1(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@@H](O)[C@H](O)CO)O1

Standard InChI:  InChI=1S/C12H21NO9/c1-5(15)13-8-6(16)3-12(21-2,11(19)20)22-10(8)9(18)7(17)4-14/h6-10,14,16-18H,3-4H2,1-2H3,(H,13,15)(H,19,20)/t6-,7+,8+,9-,10+,12+/m0/s1

Standard InChI Key:  NJRVVFURCKKXOD-VCXOXUAUSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  1  0  0  0  0  0999 V2000
    1.3153  -20.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6090  -19.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1075  -20.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1203  -20.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5897  -21.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3124  -20.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8161  -19.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491  -20.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2693  -21.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5375  -20.0481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783  -22.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1418  -22.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2870  -22.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505  -22.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1531  -23.3678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391  -21.2956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5706  -22.5232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1292  -21.7208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250  -19.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7434  -20.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170  -18.8459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250  -20.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0246  -21.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5 11  1  0
  3  4  1  0
 11 12  1  0
  4  5  1  0
 11 13  1  1
  5  6  1  0
 12 14  1  0
  1  2  1  0
 12 15  1  6
  3  7  1  1
  4 16  1  6
 14 17  1  0
  5 18  1  6
 16  8  1  0
  1 19  1  6
 19 20  1  0
  8  9  1  0
 19 21  2  0
  1  6  1  0
  1 22  1  0
  8 10  2  0
 22 23  1  0
  2  3  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1206203

   sodium;(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-methoxy-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

2. Parent:

   

   ALA1206203

   (2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-methoxy-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 323.30

Molecular Weight (Monoisotopic): 323.1216

AlogP: -3.22

#Rotatable Bonds: 6

Polar Surface Area: 165.78

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.07

CX Basic pKa: ┄

CX LogP: -2.92

CX LogD: -6.39

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.29

Np Likeness Score: 1.35

References

1. Nagy JO, Wang P, Gilbert JH, Schaefer ME, Hill TG, Callstrom MR, Bednarski MD..  (1992)  Carbohydrate materials bearing neuraminidase-resistant C-glycosides of sialic acid strongly inhibit the in vitro infectivity of influenza virus.,  35  (23): [PMID:1447751] [10.1021/jm00101a031]

Source

Source(1):

• Scientific Literature